organic compounds
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The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinylidene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O—H group forms an intramolecular O—HN hydrogen bond. In the crystal, pairs of N—HN and C—HO hydrogen bonds link neighbouring molecules into centrosymmetric dimers. These dimers are interconnected by means of three types of π–π stacking interactions. One, with a centroid–centroid distance of 3.577 (1) Å [interplanar separation = 3.4673 (6) Å], connects adjacent molecules into centrosymmetric dimers. The other two interactions, on the outward facing sides of the dimers, are between phenol rings of neighboring molecules [centroid–centroid separation = 3.7907 (13) Å and interplanar separation = 3.5071 (8) Å], and between phthalazin units [centroid–centroid separation = 3.6001 (12) Å and interplanar separation = 3.4891 (7) Å]. In combination, the π–π interactions lead to the formation of infinite layers with molecules stacked along [0-11]. These layers are, in turn, connected with neighbouring layers through the N—HN and C—HO hydrogen bonds, yielding a three-dimensional supramolecular architecture.